WO2021033980A1 - Nouveau composé et dispositif électroluminescent organique l'utilisant - Google Patents

Nouveau composé et dispositif électroluminescent organique l'utilisant Download PDF

Info

Publication number
WO2021033980A1
WO2021033980A1 PCT/KR2020/010538 KR2020010538W WO2021033980A1 WO 2021033980 A1 WO2021033980 A1 WO 2021033980A1 KR 2020010538 W KR2020010538 W KR 2020010538W WO 2021033980 A1 WO2021033980 A1 WO 2021033980A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
compound
substituted
unsubstituted
formula
Prior art date
Application number
PCT/KR2020/010538
Other languages
English (en)
Korean (ko)
Inventor
서상덕
이동훈
김민준
김영석
김동희
오중석
김서연
이다정
최승원
심재훈
Original Assignee
주식회사 엘지화학
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020200099129A external-priority patent/KR102455462B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN202080019642.XA priority Critical patent/CN113544133B/zh
Publication of WO2021033980A1 publication Critical patent/WO2021033980A1/fr

Links

Images

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
  • An organic light-emitting device using the organic light-emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode, and an organic material layer between the anode and the cathode.
  • the organic material layer is often made of a multi-layered structure made of different materials in order to increase the efficiency and stability of the organic light-emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.
  • the present invention provides a material for a novel organic light-emitting device that can be used in an organic light-emitting device and at the same time in a solution process.
  • Patent Document 1 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by the following formula 1:
  • X is O or S
  • L is a single bond; Substituted or unsubstituted C 6-60 arylene; C 2-60 heteroarylene containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S; and,
  • R 1 , R 2 , R 3 , and R 4 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 1-60 alkoxy; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 2-60 alkynyl; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 6-60 aryl; C 2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; Substituted or unsubstituted tri(C 1-60 alkyl)silyl; Or a substituted or unsubstituted tri(C 6-60 aryl)silyl, or two adjacent substituents are bonded to form a C 6-60 aromatic
  • n1 is an integer from 0 to 2
  • n2 to n4 are each independently an integer of 0 to 3
  • Ar 1 is represented by the following formula (2),
  • Ar 2 is substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S; and,
  • V 1 to V 4 are each independently CR a or N,
  • W 1 and W 2 are each independently a single bond, CR b , O or S,
  • R a and R b are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S; Or, or two adjacent R a , or two adjacent R b are bonded to each other to C 6- 60 forms an aromatic ring,
  • p is an integer of 0 or 1.
  • the present invention the first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Formula 1, wherein the organic light-emitting device comprises: to provide.
  • the compound represented by Chemical Formula 1 may be used as a material for an organic material layer of an organic light-emitting device, and may improve efficiency, low driving voltage, and/or lifetime characteristics in the organic light-emitting device.
  • FIG. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 is an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron injection and transport layer 8, and a cathode 4 Is shown.
  • substituted or unsubstituted refers to deuterium; Halogen group; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or it means substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more substituent
  • a substituent to which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent to which two phenyl groups are connected.
  • the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the ester group may be substituted with an oxygen of the ester group with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms.
  • it may be a compound of the following structural formula, but is not limited thereto.
  • the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
  • the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cycloheptylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhex
  • the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
  • the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • Etc When the fluorenyl group is substituted, Etc.
  • Etc it is not limited thereto.
  • heteroaryl is a heteroaryl containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heteroaryl include xanthene, thioxanthen, thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, Pyrimidyl group, triazine group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino Pyrazinyl group, isoquinoline group
  • the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group, and arylsilyl group is the same as the example of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the aforementioned alkyl group.
  • heteroaryl among heteroarylamines the above-described description of heteroaryl may be applied.
  • the alkenyl group of the aralkenyl group is the same as the example of the alkenyl group described above.
  • the description of the aryl group described above may be applied except that the arylene is a divalent group.
  • the description of the above-described heteroaryl may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the aryl group or the cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents.
  • the heteroaryl is not a monovalent group, and the description of the above-described heteroaryl may be applied except that two substituents are bonded to each other.
  • the present invention provides a compound represented by Chemical Formula 1.
  • L is a single bond.
  • R 1 , R 2 , R 3 and R 4 are hydrogen. At this time, preferably, n1 to n4 are 0.
  • one of R 1 , R 2 , R 3 and R 4 is phenyl or pyridinyl and the other is hydrogen.
  • one of n1 to n4 is 1, and the others are 0.
  • two adjacent R 1 , two adjacent R 2 , two adjacent R 3 , or two adjacent R 4 are bonded to each other to form a benzene ring, and the remaining R 1 to R 4 are hydrogen.
  • Ar 1 is preferably any one selected from the group consisting of the following Formulas 2-1 to 2-3:
  • Ar 2 is as defined in Formula 1,
  • R a1 , R a2 and R a3 are each independently hydrogen or deuterium; Or two adjacent R a1 , two adjacent R a2 , or two adjacent R a3 bonded to each other to form a benzene ring, and the rest is hydrogen,
  • Each R b1 is independently hydrogen or deuterium
  • W 3 and W 4 are each independently O or S,
  • p is an integer of 0 or 1.
  • Ar 1 is any one selected from the group consisting of:
  • Ar 2 is as defined in Chemical Formula 1,
  • W 3 and W 4 are each independently O or S.
  • Ar 2 is phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, dibenzofuranyl, di Benzothiophenyl, carbazol-9-yl, or 9-phenyl-carbazolyl, and Ar 2 is unsubstituted or substituted with one or more deuterium.
  • the present invention provides a method for preparing a compound represented by Formula 1, such as the following Scheme 1 as an example:
  • X, L, and Ar 2 are as defined in Formula 1
  • Y 1 and Y 2 are each independently a halogen group such as chloro or boromo
  • Z is a boronic acid group, a boronic acid ester group, or It is a boron-containing organic group such as a boronic acid pinacol ester group
  • Ar 1 ′ is a substituent having the following structure
  • V 1 to V 4 , W 1 and W 2 are as defined in Formula 1.
  • compound (1) of Formula 1 is a palladium-catalyzed coupling reaction between a compound (i) having a parental structure and a compound (ii) including an electron acceptor substituent bonded to the parental structure, and compound (iii) Manufacturing a; And it can be prepared by a production method comprising the step of subjecting the compound (iii) to a Suzuki coupling reaction in the presence of a compound (iv) containing an organic group containing boron and a base and a palladium catalyst.
  • the palladium catalyzed coupling reaction and the Suzuki coupling reaction may be carried out in the presence of a base, and at this time, the base is sodium tert-butoxide, potassium tert-butoxide. -butoxide), sodium tert-pentoxide, sodium ethoxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride hydride), lithium hydride, or potassium hydride;
  • Organic bases such as tetraethylammonium hydroxide ((Et 4 NOH), bis(tetraethylammonium) carbonate, triethylamine; inorganic salts such as cesium fluoride, and any one or a mixture of two or more of them may be used.
  • I can.
  • the palladium catalyzed coupling reaction may be performed in an organic solvent, and the Suzuki coupling reaction may be performed in water as a solvent.
  • organic solvent diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol diethyl ether, dimethoxyethane, bis(2-methoxyethyl) ether, diethylene glycol diethyl ether, tetrahydro Ether solvents such as furan or anisole; Aromatic hydrocarbon-based solvents such as benzene, toluene or xylene; Halogenated aromatic solvents such as chlorobenzene, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, dimethylimidazolidone or acetonitrile; Or a sulfoxide-based solvent such as dimethyl sulfoxide (DMSO), and any one or a mixture of two or more of them may be used.
  • DMSO dimethyl sulfoxide
  • reactants used in the preparation of compound (1) of Formula 1 may be prepared by using a conventional organic reaction, or may be obtained and used commercially.
  • the compound (i) having the parental structure may be prepared in the same manner as in Scheme 2 below.
  • Reaction Scheme 2 below is only an example for explaining the present invention, but the present invention is not limited thereto.
  • X is O or S
  • Y is a halogen group such as bromo
  • the present invention provides an organic light-emitting device including the compound represented by Chemical Formula 1.
  • the present invention provides a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound according to the present invention.
  • the organic light-emitting device according to the present invention may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • the compound represented by Formula 1 may be included in the emission layer.
  • the compound represented by Formula 1 may be included in the hole injection layer, the hole transport layer, or the emission layer.
  • an electron blocking layer (not shown) may be further included between the hole transport layer and the emission layer, and a hole blocking layer (not shown) may be further included between the emission layer and the electron injection and transport layer.
  • the organic light emitting device according to the present invention can be manufactured using materials and methods known in the art, except for using the compound according to the present invention.
  • the organic light-emitting device may be manufactured by sequentially laminating an anode, an organic material layer, and a cathode on a substrate.
  • the anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate.
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron injection and transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890).
  • the manufacturing method is not limited thereto.
  • an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the cathode material a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer.
  • the cathode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO:Al or SNO 2 :Sb; Conductive compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the hole injection layer is a layer that injects holes from an electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for a light emitting layer or a light emitting material.
  • a compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable.
  • the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes.
  • the material is suitable. Specific examples include an arylamine-based organic material, a conductive compound, and a block copolymer having a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • the organic light emitting device may further include an electron blocking layer selectively on the hole transport layer.
  • the electron blocking layer is formed on the hole transport layer, and is preferably provided in contact with the light emitting layer to control hole mobility and prevent excessive movement of electrons, thereby increasing the probability of hole-electron coupling, thereby increasing the efficiency of the organic light-emitting device. It refers to the layer that plays a role in improving the value.
  • the electron blocking layer includes an electron blocking material, and an arylamine-based organic material may be used as an example of the electron blocking material, but is not limited thereto.
  • the emission layer may include a host material and a dopant material.
  • Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group
  • the styrylamine compound is substituted or unsubstituted
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group
  • the styrylamine compound is substituted or unsubstituted
  • at least one arylvinyl group is substituted on the arylamine, one or two or more substituents selected from the group consisting
  • the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
  • the organic light emitting device may further include a hole blocking layer selectively on the emission layer.
  • the hole blocking layer is formed on the light emitting layer, preferably provided in contact with the light emitting layer, to improve the efficiency of the organic light emitting device by increasing the probability of hole-electron coupling by controlling electron mobility and preventing excessive movement of holes. It means the layer that plays a role.
  • the hole-blocking layer includes a hole-blocking material, and examples of the hole-blocking material include: a subazine derivative including triazine; Triazole derivatives; Oxadiazole derivatives; Phenanthroline derivatives; A compound into which an electron withdrawing group such as a phosphine oxide derivative has been introduced may be used, but is not limited thereto.
  • An electron transport layer is formed on the emission layer or on the hole blocking layer.
  • the electron transport layer is a layer that receives electrons from the cathode or an electron injection layer to be described later and transports electrons to the emission layer.
  • As an electron transport material electrons are well injected from the cathode and can be transferred to the emission layer. Larger materials are suitable. Specific examples include pyridine derivatives; Pyrimidine derivatives; Triazole derivatives; Al complex of 8-hydroxyquinoline; Complexes containing Alq 3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron injection layer is a layer located between the electron transport layer and the cathode to inject electrons from the cathode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or the light emitting material. It has, and prevents the movement of excitons generated in the light-emitting layer to the hole injection layer, and also, a compound excellent in the ability to form a thin film is preferable.
  • the metal complex compound examples include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.
  • the electron transport layer and the electron injection layer may be provided in the form of an electron transport layer for transporting received electrons to the light emitting layer and an electron injection and transport layer that simultaneously functions as an electron injection layer.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • the compound according to the present invention may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • Dibenzo[b,d]furan-1-ylboronic acid (25.0g, 117.9mmol) and 1-bromo-2-nitronaphthalene (32.7g, 129.7mmol) were dissolved in Tetrahydrofuran (THF) 255ml, and in the resulting mixed solution, A solution in which potassium carbonate (65.2 g, 471.7 mmol) was dissolved in 125 ml of H 2 O was added.
  • tetrakis(triphenylphosphine)palladium(0) Pd(PPh 3 ) 4 , 6.8g, 5.9mmol
  • a glass substrate on which ITO (Indium Tin Oxide) was deposited to a thickness of 1,400 ⁇ was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.
  • the following HI-A and hexaazatriphenylene (HAT-CN) were sequentially thermally vacuum deposited to a thickness of 800 ⁇ and 50 ⁇ , respectively, to form a hole injection layer.
  • the following HT-A was vacuum-deposited to a thickness of 800 ⁇ as a hole transport layer
  • EB-A was thermally vacuum-deposited to a thickness of 600 ⁇ as an electron blocking layer thereon.
  • the following host RH-A and dopant RD were mixed at a weight ratio of 98:2 and then vacuum deposited to a thickness of 400 ⁇ to form a light emitting layer.
  • ET-A and Liq were mixed at a weight ratio of 1:1 and thermally vacuum deposited to a thickness of 360 ⁇ , and Liq was vacuum deposited thereon to a thickness of 5 ⁇ to form an electron injection layer.
  • magnesium and silver were sequentially mixed at a weight ratio of 10:1 and deposited to a thickness of 220 ⁇ , and aluminum was deposited thereon to a thickness of 1000 ⁇ to form a cathode, thereby manufacturing an organic light-emitting device.
  • LT97 driving voltage, current efficiency, and lifetime
  • Example 1 Compound 1 4.54 22.5 110 Example 2 Compound 2 4.53 22.3 121 Example 3 Compound 3 4.56 22.0 123 Example 4 Compound 4 4.61 22.8 111 Example 5 Compound 5 4.58 22.1 108 Example 6 Compound 6 4.53 21.3 97 Example 7 Compound 7 4.56 22.6 101 Example 8 Compound 8 4.76 23.1 106 Example 9 Compound 9 4.71 23.0 104 Example 10 Compound 10 4.73 23.3 108 Example 11 Compound 11 4.58 22.1 132 Example 12 Compound 12 4.65 22.9 95 Comparative Example 1 RH-A 5.10 18.3 65 Comparative Example 2 RH-B 5.15 20.9 83 Comparative Example 3 RH-C 5.81 12.3 46
  • Compounds RH-B and RH-C used in Comparative Examples 2 and 3 are compounds each having the following structure.
  • the compound represented by Formula 1 has a structure in which the structure of Formula 2 serves as an electron acceptor and a parental structure that serves as an electron donor are connected.
  • the parental structure serving as an electron donor exhibits high stability by condensing both benzocarbazole and benzofuran or benzothiophene to form a ring.
  • the structure in which the unit serving as an electron acceptor has two nitrogen atoms facing each other in the form of pyrazine, as in the structure of Formula 2, has a stronger electron pulling property than the quinazoline structure applied in the Comparative Example. Show.
  • substrate 2 anode

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le comprenant.
PCT/KR2020/010538 2019-08-20 2020-08-10 Nouveau composé et dispositif électroluminescent organique l'utilisant WO2021033980A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202080019642.XA CN113544133B (zh) 2019-08-20 2020-08-10 化合物及利用其的有机发光器件

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2019-0101898 2019-08-20
KR20190101898 2019-08-20
KR1020200099129A KR102455462B1 (ko) 2019-08-20 2020-08-07 신규한 화합물 및 이를 이용한 유기 발광 소자
KR10-2020-0099129 2020-08-07

Publications (1)

Publication Number Publication Date
WO2021033980A1 true WO2021033980A1 (fr) 2021-02-25

Family

ID=74660544

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2020/010538 WO2021033980A1 (fr) 2019-08-20 2020-08-10 Nouveau composé et dispositif électroluminescent organique l'utilisant

Country Status (1)

Country Link
WO (1) WO2021033980A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112979536A (zh) * 2021-03-12 2021-06-18 吉林奥来德光电材料股份有限公司 一种磷光主体材料及其制备方法和有机电致发光器件

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140097044A (ko) * 2013-01-29 2014-08-06 주식회사 엘지화학 헤테로환 화합물 및 이를 포함한 유기 전자소자
KR101478990B1 (ko) * 2013-12-27 2015-01-06 롬엔드하스전자재료코리아유한회사 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20150121337A (ko) * 2014-04-18 2015-10-29 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20180008286A (ko) * 2016-07-14 2018-01-24 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20190010499A (ko) * 2017-07-20 2019-01-30 주식회사 엘지화학 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140097044A (ko) * 2013-01-29 2014-08-06 주식회사 엘지화학 헤테로환 화합물 및 이를 포함한 유기 전자소자
KR101478990B1 (ko) * 2013-12-27 2015-01-06 롬엔드하스전자재료코리아유한회사 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20150121337A (ko) * 2014-04-18 2015-10-29 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20180008286A (ko) * 2016-07-14 2018-01-24 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20190010499A (ko) * 2017-07-20 2019-01-30 주식회사 엘지화학 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112979536A (zh) * 2021-03-12 2021-06-18 吉林奥来德光电材料股份有限公司 一种磷光主体材料及其制备方法和有机电致发光器件

Similar Documents

Publication Publication Date Title
WO2021025328A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2021080368A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2020111733A1 (fr) Dispositif électroluminescent organique
WO2020171531A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2019240473A1 (fr) Composé et diode électroluminescente organique le comprenant
WO2020149596A1 (fr) Nouveau composé et diode électroluminescente organique l'utilisant
WO2021091173A1 (fr) Nouveau composé et dispositif électroluminescent organique faisant appel à celui-ci
WO2021125648A1 (fr) Nouveau composé, et élément électroluminescent organique l'utilisant
WO2021080254A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2021080253A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2021066351A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2022235101A1 (fr) Dispositif électroluminescent organique
WO2021033980A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2022031028A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2022031013A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2022031016A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2022059923A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2021040467A1 (fr) Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant
WO2021029715A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2021210774A1 (fr) Nouveau composé et élément électroluminescent organique le comprenant
WO2021149954A1 (fr) Dispositif électroluminescent organique
WO2020149656A1 (fr) Nouveau composé et diode électroluminescente organique l'utilisant
WO2021066350A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2020185054A9 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2020171530A1 (fr) Composé et dispositif électroluminescent organique le comprenant

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 20855172

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 20855172

Country of ref document: EP

Kind code of ref document: A1